Things to Do in January in Chicago (2019)

This post lists top things to do in January in Chicago as well as things to do at night, free activities and family friendly events.

Start the New Year right with a trip to the Windy City. January in Chicago is full of events, most of which will keep you indoors.  If you are willing to brave the cold, January is a great month to see Chicago. 


This section covers our top ten list for January. When possible, we’ve noted activities that are free or kid-friendly. For more ideas on popular things to do in Chicago, check out our posts on bus tours and walking tours of the city.

Some of the items listed in this post are included for free with the purchase of a tourist discount pass

While most of the holiday traditions wrap up within the first week of the new year, there is still a full calendar to keep locals and guests entertained. Below we have included some of our favorite traditions, but for a more complete calendar for January in Chicago look here.

Things to Do in January in Chicago1. Ice Skating 

Ice Skating is a great way to spend the day or evening hours, especially with numerous rinks around the city.

There is the McCormick Tribune Ice Rink in Millennium Park. Right underneath the Bean and on the edge of the downtown area makes this a perfect spot, and you can warm up with some hot chocolate served right next to the rink. 

Across the bridge in Maggie Daley Park you will find the Skating Ribbon.  Surrounding the rock wall and with skyline in the background, this is a “skating through the alpines” experience. 

For both rinks, skating is free and rentals are $12 on weekdays, $14 on weekends.

2. New Years Day 5K

January 1st 
Lincoln Park 

Start the New Year off on the right foot with the New Years Day 5K Run/Walk.  The race begins and ends in the south part of Lincoln Park.

3. Maxwell Street Market

Sundays 7am-3pm 
On Desplaines from Polk to Taylor St.

Bundle up to enjoy the international flare at this market on Sunday mornings that has been a Chicago tradition for over 100 years.  Take in the bargains and culture at this year round market.

4. Sketch Comedy Festival

January 10-20
Stage 773 1225 W. Belmont

Perfect for the Comedy Capital of the world, this festive highlights over 1,000 performers in the 180+ shows that take place during these 10 days. Founded in 2002 with just 35 local performers, this has now become the largest of its kind in the world, drawing in writers and performers from across the globe.

5. Cubs Convention

January 18-20, 2019
Grand Sheraton Hotel 

This annual event has a whole new meaning now that our lovable-losers are now the2016 World Series Champions.  Come meet some of the players and take in all things Cubs.

6. Tomorrow Never Knows Music Festival

January 16-20, 2019

For a decade, people have been braving the January weather for this music festival.  This festival celebrates up-and-coming local indie artists, as well as draws in national acts, musicians and comedians a like. Hosted in different independent venues across this city, this provides a true Chicago experience.

7. SoxFest 2018

January 25-27, 2019
Hilton Chicago 

For the 27th year, fans can come and celebrate the White Sox through meeting players, current and past, in an interactive space while celebrating the team and season.

8. Restaurant Week 

January 25 -February 7, 2019

This is the perfect opportunity to try some favorite Chicago restaurants.  Hundreds of restaurants participate during these two weeks, providing multiple course meals with a prix fixe menus.  Enjoy these dining deals that show off the rich culinary city that Chicago is.

9. Winter Brew

January 26, 2019
DANK Haus German American Cultural Center

The Chicago Street Festivals transform to indoors during the winter for traditions such as Winter Brew.  Local breweries across the city participate for this annual event, showcasing a few of their craft beers and provide limited release options.

10. Go to a Game

Both the NHL Chicago Blackhawks and NFL “‘DAAAA Bears” are playing home games this month and each venue is located downtown and easily accessible for travellers. Use this chance to watch a professional sports game and cheer on the home team!

You can get discounted tickets via StubHub for any game that fits your schedule!

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There are a number of things to do in Chicago at night. For additional ideas on how to spend your evening, make sure to check out our master Things to do at Night in Chicago post.

Adler After Dark

January 17, 2019
General Admission Tickets: $20 in advance, 25 at the door 

This tradition returns on January 17th.  Guests 21+ can enjoy the planetarium after hours with drinks and unlimited entertainment.  Escape the cold and enjoy this monthly event.

Catch a Comedy Show

With Chicago being the comedy capital of the world, this is a perfect event for some night time entertainment. Beyond the Sketch Comedy Festival, there are many spots to catch a good laugh. With popular show options such as Second City and iO, you are such to catch a show to fit your budget and your interest.

Grab a Drink at a Speakeasy 

Warm up with some crafty cocktails at one of our numerous hidden bars throughout the city.  Infamous for its 1920’s gangster history, this is a perfect way to experience Chicago.  Some of these bars even provide live entertainment. 

Check here for a guide to some of the best speakeasy bars and how to find them.

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With a little planning, there are a lot of free activities available to do in Chicago. Some of the events we’ve mentioned in this post like our walking tours are free of charge! Here are a few more ideas for free activities in January but for our comprehensive list, visitin our Free Things to Do in Chicago post

A great way to visit Chicago on a budget is with a Tourist Discount Pass. Find out how you can enter many top attractions for free.

Check out the Chicago Cultural Center

This beautiful and historic building is free and open for the public to explore. Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here. 

Check out their calendar of events to see what is going on during your visit.

Play at The Beach

January 19, 2019- February 3, 2019

Sounds like a weird suggestion for January, but this is an indoor beach made of plastic balls. Think of it as a giant ball pit with deck chairs, lifeguard chairs, umbrellas and signage that mimic the sensation of a day at the beach.

It is open most days at Navy Pier from 11am-8pm, but get all the details here.

Go to the Game Room at the Chicago Athletic Association

Inside the historic Chicago Athletic Association building you will find much more than a luxury hotel. On the second floor, there is a Game Room with shuffleboard, pool tables, foosball, and bocce. All free to use, find the game master to make a reservation while you enjoy something to sip on.

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Some of our Top Ten are great activities for children, but check out our post about Family Friendly Activities in Chicago for a more complete guide.  Below you will find a couple other options to keep your children entertained this month!

Visit the Chicago Children’s Museum at a Discount

At the Chicago Children’s Museum at Navy Pier, Play Late Thursdays begins on January 3, 2019 in which up to four people can enter the museum for the price of one ticket ($14.95) from 4-8pm.

If Thursdays don’t fit your schedule, you can get free admission with a Chicago Discount Tourist Pass.

This event is every Thursday but on the first Thursday of the month, kids take center stage with programs including:

  • Open mic nights with guest MC’s to run the show
  • Themed dance parties for the whole family
  • Kid-friendly and kid-starring performances


Lincoln Park Zoo: 2001 N Clark St
Open until January 6, 2019

The Lincoln Park Zoo lights up at night with millions of holiday lights! Be one of the first 1000 people through the gates to receive special glasses to view the lights through. Beyond elaborate light displays, you will discover live ice carving, festive music, train rides, an ice skating rink, and food.  So bundle up, grab a hot beverage, and enjoy one of the city’s favorite traditions.

Winter WonderFest

Navy Pier 

Enjoy this indoor festive playground as it returns for the 18th year! The Festival Hall at Navy Pier is transformed into a Winter Wonderland with carnival rides and activities.  This festival runs until January 6th.

Go to a Themed Restaurant or Park!  

Not too far from the city, there are a few really neat theme parks.  Six Flag Great America is a favorite for older kids since it has amazing roller coasters.  With admission, there is an attached water park called Hurricane Harbor. Key Lime Cove is an indoor water park nearby if you are looking for fun in the winter.  There is also a Medieval Times nearby if you want to enjoy a meal while watching knights joust.

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